Chicago: could it now be one of my most favourite cities?? We spent a jam-packed weekend there and barely squeezed in everything that I wanted to do. Although all my friends and colleagues had raved about the Windy City, I wasn’t expecting to be so enamoured with it. The city feels like it has the culture and sophistication of New York – but without all the people. If you’re a first-timer to Chicago, or an experienced visitor looking for some new ideas, here’s a guide of what to do and what to eat in Chicago in a weekend.

What to do and what to eat in Chicago in a weekend

Eat

A trip to Chicago isn’t complete without trying the pizza. Chicago is famous for its deep-dish pizza and you can count on an argument if you ask Chicagoans for the best place. To avoid a squabble, plan on trying a few pizza joints and then make up your own mind. After much research, we made our way to Pequod’s Pizza. This always-busy place is known for its deep-dish pizza with a delicious caramelized crust. The crust comes from the thin layer of cheese they sprinkle along the edge of the dough before it’s put in the super-hot oven. Insider’s tip: While you can’t make a reservation at Pequod’s, you can do a “table request” on their website if you plan ahead.

Other highly recommended places are Lou Malnati’s, Gino’s East and Giordano’s.

What to do and what to eat in Chicago in a weekend | Rebecca and the World

We also found out that Chicago even has its own style of hot dog. The best place to try it is at Portillo’s. A Chicago hot dog is a beef frankfurter topped with yellow mustard, chopped onions, sweet pickle relish, tomato, a dill pickle, pickled sport peppers and celery salt. And it was actually pretty tasty. Apparently, no ketchup allowed!

If you do go to Portillo’s don’t miss the chocolate cake shake – a chocolate milkshake literally full of chunks of chocolate cake. Seriously.

What to do and what to eat in Chicago in a weekend | Rebecca and the World

Chicago isn’t all about fast food, though.

The Publican’s menu is farmhouse-inspired and diners sit at huge communal tables. We were actually sat at the bar right outside the door to the kitchen, so could see all the food as it was brought out. The atmosphere is noisy and jovial and perfect for a night out with a group of friends.

Next on the list was avec restaurant. The menu is focused on tapas-style Mediterranean dishes, so we were able to try a number of different items. Another restaurant with communal-style seating, we ended up sharing a table with a lovely Mexican couple and their young daughter, and got to try even more plates after they realised they’d over-ordered.

The Duck Inn isn’t located in the coolest part of town, but it does serve a killer brunch. You’re definitely not coming here for a healthy start to the day – you’re coming to sample some delicious food in a cosy environment.

What to do and what to eat in Chicago in a weekend | Rebecca and the World

Our last meal was burgers at Au Cheval. No reservations, so get here early and get your name in the queue – even on a Monday at 11.30am the place was packed. The burgers here are totally worth the calories, as are the delicious cocktails.

What to do and what to eat in Chicago in a weekend | Rebecca and the World

There was just not enough time to eat at all the restaurants I had on my list. Stay tuned for more eating recommendations when we return.

See

I have no idea about architecture, but what I do know is that Chicago is freaking beautiful. On every corner you will see the vision of acclaimed architects played out in a variety of different materials and styles. The best way to see this is from the water. Take a river cruise with the Chicago Architecture Foundation to get a crash course in architecture and the history of the city. The 90-minute cruises are led by volunteers who provide entertaining and informative commentary. An absolute must-do.

What to do and what to eat in Chicago in a weekend | Rebecca and the World

What to do and what to eat in Chicago in a weekend | Rebecca and the World

What to do and what to eat in Chicago in a weekend | Rebecca and the World

What to do and what to eat in Chicago in a weekend | Rebecca and the World

Back on land, walk the pedestrian Riverwalk, a paved, 1.25 mile stretch. We walked a short section of it but were in a hurry to get to our river cruise, so we unfortunately didn’t have time to stop at all the lovely bars that were full of people enjoying the sunshine.

We didn’t have the time, but Chicago is of course home to many of Frank Lloyd Wright’s famous designs.

We stayed close to Millenium Park, a huge public space that hosts concerts during summer. Join the crowds for a selfie at Cloud Gate, aka The Bean. If you want to avoid the crowds, plan to visit in the morning.

What to do and what to eat in Chicago in a weekend | Rebecca and the World

What to do and what to eat in Chicago in a weekend | Rebecca and the World

What to do and what to eat in Chicago in a weekend | Rebecca and the World

Chicago is located on Lake Michigan and has a number of beaches dotted around the city. Every city should have a beach, in my opinion. It wasn’t quite warm enough for us to even dip our toe in the water, but in summer the sand is packed with beach-goers. You can also burn off all those pizza calories along the paved 18-mile lakefront trail.

What to do and what to eat in Chicago in a weekend | Rebecca and the World

What to do and what to eat in Chicago in a weekend | Rebecca and the World

If you’re into art, The Art Institute of Chicago houses an enormous collection. It has in past years been voted the number one museum in the world. Art lovers could spend hours or even days wandering through each of the exhibits. It’s conveniently located next to Millenium Park.

What to do and what to eat in Chicago in a weekend | Rebecca and the World

What to do and what to eat in Chicago in a weekend | Rebecca and the World

What to do and what to eat in Chicago in a weekend | Rebecca and the World

Play

Chicago is home to The Second City, an improv comedy club that launched the careers of the likes of Tina Fey, Mike Myers and Martin Short. The club showcases some of the funniest sketches I have ever seen, and I was blown away by the comedians’ improv skills. Be prepared for audience participation!

What to do and what to eat in Chicago in a weekend | Rebecca and the World

For great views over Millenium Park, stop by Cindy’s Rooftop for a drink or a bite to eat. The Signature Lounge on the 96th floor of the John Hancock building is also famous for its city views.

What to do and what to eat in Chicago in a weekend | Rebecca and the World

Chicago is one of the homes of blues music, and a fun night out if you’re a music fan. As I researched, I found that most of the shows on the nights we were there were more jazz-focused, so we went to Buddy Guy’s Legends and watched a toe-tappin’ blues show from our own table.

What to do and what to eat in Chicago in a weekend | Rebecca and the World

We didn’t get to a lot of bars on our trip (we’re getting oooold, man!) but we did stumble upon Moneygun while we were waiting for our table at avec. Intimate, with an extensive and well-priced cocktail list, it felt super secret and hidden. Some recommended bars I did find during my online research include Three Dots and a Dash, The Broken Shaker and The Aviary.

Stay

There are a tonne of places to stay in Chicago, but as we were celebrating a special weekend – my husband’s birthday – we splashed out and stayed at theWit. It’s stylish, close to both Millenium Park and the river, and the staff organised cupcakes and glasses of bubbles for Matt’s birthday. What more could we ask for?

 

What are your favourite things to do in Chicago?

 

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What to do and what to see in Chicago in one weekend | Rebecca and the World